Daytime
$62.00 (Ticket)
+
$3.75 (Booking Fee)
+
$6.20
(A&A Tax)
$65.00 (Ticket)
+
$3.75 (Booking Fee)
+
$6.50
(A&A Tax)
$69.00 (Ticket)
+
$3.75 (Booking Fee)
+
$6.90
(A&A Tax)
Includes a complimentary soda or water.
Everyone has loved having more room, so we are staying at just 30 people per cruise (instead of 48).
Tickets go on sale 6 days prior to the date you want to sail.
April 13 – april 23, seven days a week.
12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail) * * Friday, Saturday & Sunday only
12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail)
11:00 am – 1:00 pm 1:30 pm – 3:30 pm 4:00 pm – 6:00 pm 6:30 pm – 8:30 pm (Sunset Sail)
10:00 am – 12:00 pm (Saturday & Sunday Only) 12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail)
11:00 am – 1:00 pm 1:30 pm – 3:30 pm 4:00 pm – 6:00 pm
No 2 hour public sails due to US Boat Shows Private Charters are available
October 10 – October 14 we will be sailing from the US Sailboat Show
We sail rain or shine, unless the captain cancels the cruise due to unsafe conditions. We offer complimentary rain ponchos in case of rain.
Please visit our frequently asked questions page.
Learn to Sail the Annapolis Way
Which course is right for me.
I want to be able to operate a vessel I already own or intend to buy.
I intend on renting or chartering sailboats in the future.
I want to explore the art of sailing and am looking for a great experience.
I'm looking to learn at my own pace with personalized private instruction.
We provide a community at the Annapolis Sailing School for your ongoing growth and enjoyment. We offer day sailboat rentals, adult sailing, KeelBoat Club Membership, KidShip sailing, powerboat lessons, and events at our beautiful location on Bembe Beach.
@annapolissailingschool
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The Waypoints Annapolis base is in the heart of Annapolis right in the middle of the sailing capital of the world. The Chesapeake Bay, at about 200 miles long, is the largest estuary in the United States. There are coves and inlets all along the shoreline, small quaint towns to explore, and plenty of places to anchor or dock with history all around you as you explore national landmarks.
Your destinations on the Chesapeake Bay are boundless. Make sure to allow time to visit downtown Annapolis at the beginning or end of your charter. Here you will find Main St. and small side streets loaded with shops, restaurants, galleries, and the Market House. And if time allows, take a stroll through the Naval Academy. Whatever you choose, you cannot go wrong in this historic town.
Sailing Itineraries are helpful when planning your charter. You can choose the North or the South route. North takes you to historic Baltimore Harbor with nice quiet anchorages along the way. Sailing the South route will take you to places such as the legendary St. Michaels and the historical landmarks in Oxford and Cambridge.
So many destinations on the Bay to explore makes Annapolis a great choice for your charter vacation.
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Annapolis Fall Charter Special. Get One Night FREE!*
Welcome to south river boat rentals, boat rentals and charters on the chesapeake bay, family, social & corporate outings.
We had a FANTASTIC time on the Bennington boat. Our Captain Max was a blast! He found multiple spots for us to hang out in the water, and even drove us around tubing! 10/10 recommend for your Annapolis boat rental!
We offer water sports – tubing, skiing, wakeboarding, and kneeboarding.
Water Sports on the Chesapeake Bay bring all of your family and friends together. Whether you enjoy water skiing, wakeboarding, tubing, or knee boarding, we have the water sports for you on the Chesapeake Bay.
1/2 day: $550 | full day: $900, 6 max / wt limit: 1410 lbs.
6 max / wt limit: 1250 lbs.
1/2 day: $800 | full day: $1400, 12 max/wt limit 2200 lbs..
10 max/wt limit 2600 lbs..
12 max/ wt limit 2400 lbs..
1/2 day: $950 | full day: $1700, 10 max including our captain.
30 max passengers / includes captain.
12 max passengers / includes captain.
Just Google "South River Boat Rentals" to see all the positive reviews we have earned throughout the years. Customer service and ensuring you have an excellent day on the water is our top priority.
We used South River boat rentals this past weekend for a bachelorette party and had the absolute best time. Special thanks to Captain Chris and the rest of the crew who were all kind, courteous, and informative. Definitely will be returning! - Gabby Cooper
Amazing day on the pontoon boat with our extended family. Graham was a WONDERFUL captain and host. He took us to a quiet area to swim, dragged all 4 kids in the tube, and slowed the boat so we could look at wildlife up close. Worth every penny! Highly recommend requesting Graham as your captain. - Meredith Bove
Thank you for a memorable experience. Would recommend this place to everyone. Can’t wait to make another reservation in the future. A big thank you to Nancy for your amazing customer service and friendly personality!! - Nicole Wilkinson
Thank you for an amazing time. We rented the 26' Chaparral for a day of cruising and tubing. We could not be more grateful. The boat ran perfectly and the staff was king, courteous and accommodating. We will return! - Garrick Muench
Had a great experience with them. I even had to reschedule for a later date and they were able to accommodate! Would definitely recommend the 50' Trawler! - Kourtney Ramseur
Such an amazing company to work with!!! From scheduling, to weather related rescheduling, the captain, and the overall boat condition and experience - I cannot say enough good things about South River Boat Rentals! Definitely will return! - Tara Klimovitz
The boat was ready and waiting for us; the service was good from booking to returning the boat. South River made it an easy and enjoyable experience. - Judy Graham
So much fun renting a boat for the day. Our Captain Wayne was awesome and took us wherever we wanted to go. He gave suggestions based on weather/water conditions/our ideas of what we wanted to do. It was really a great day! - Sarah Edwards
Outstanding Labor Day out on the water thanks to South River Boat Rentals! Best prices in the area, great vessel, easy to use, a lot of fun for our family! - Mark Fratto
The staff was awesome and super hospitable. They walked us through everything and made sure we felt comfortable on the boat. Boat was in great condition too! - Dylan Stoskus
We had a wonderful experience with South River Boat Rental! The boat was in perfect condition, very clean, and the staff was a pleasure to work with. Would highly recommend! - Liz Gillette
View this profile on Instagram South River Boat Rentals (@ southriverboatrentals ) • Instagram photos and videos
For questions, information and details about your rental/charter please call: 410-956-9729.
COMMENTS
Captained and Bareboat Charters in Annapolis, Maryland. The Chesapeake Bay is among the world's top cruising and sailing destinations. A true American treasure, the Bay delivers a long enjoyable sailing season from early Spring to late Fall, with over 11,000 miles of shoreline to explore. From quiet, unspoiled anchorages, to historic seaside ...
Welcome Aboard! Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Located in the heart of the Chesapeake Bay, Annapolis is "America's Sailing Capital.". Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the ...
Your Dream Adventure Awaits. Catering to clients seeking a unique, private sailing adventure for up to six passengers, we offer world-class sailing yachts, decades of experience, and 5-star service to ensure that your charter is truly memorable. All our charters are for private parties, so you can have it your way.is required.
Sailing Charters in. Annapolis, MD. Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world. Minimum age: 7 years.
All Day of Sailing: come sailing on the Chesapeake Bay all day! Duration: 6 hours (leaves and returns to Annapolis) Starting at $1,550 weekdays for 2 guests. Your sailing charter includes: skipper, crew member, snacks, lunch & beverages. Please check rates and book a sailing cruise by clicking the button below. Book Now.
Sailing Charters in Annapolis MD on the Chesapeake Bay. We are a family-owned and operated company based in Annapolis Maryland, offering private sails for any occasion on Southerly, our 54 ft. Irwin.From three-hour day cruises to sunset dinner sails, to wedding proposals and photo shoots, we can customize your sailing charter for an on-the-water experience to remember.
This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay. Invite up to 12 guests for half or full-day private yacht charters. She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area. With a 5 ft draft, Muse can navigate secluded coves and anchorages. A 27-knot cruise speed ensures fast travel and ...
We provide luxury sailing yacht charters for a few hours, days or weeks in the Chesapeake Bay, Bahamas and Virgin Islands. Skip to content call now (410) 956-9323
Watermark Journey features Yacht Charters, Things to do in Annapolis and Wedding Ideas on The Chesapeake Bay-Annapolis-Baltimore. Watermark. Directions & Parking 410-268-7601 Search. Close Toggle ... Customized private yacht charters; History comes alive in our museum without walls; Family fun activities for all ages; Highly trained, certified ...
Come sail the Chesapeake Bay. Join us in Annapolis & Baltimore. We hold a current USCG Certificate of Inspection for Private charters, meaning that she is inspected in her construction, equipment, and maintenance to rigorous federal standards. SV Pintita is a 45 foot sailboat available for private charters, team-building outings in Annapolis ...
The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she's docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them. The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner ...
Half day, full day and evening sails plus special events. Make a Reservation. Annapolis Sailing Adventures, LLC. Made with Squarespace. Annapolis, Maryland. [email protected]. 858-774-5705.
Bareboat sailboat charters on the Chesapeake Bay, within easy sailing distance of Annapolis, Baltimore, Oxford, St. Michaels. Ph: 410-639-7140 Fax: 410-639-7194 [email protected]. Bareboat Sailing Charters on the Chesapeake Bay. home; Information & Reservation; Plan a Cruise;
Annapolis FAQ. Waypoints Annapolis offers a variety of new model sailing monohulls, catamarans, and powerboats for multi-day charters on the Chesapeake Bay. Our team prides itself in providing an elevated charter experience for each of our guests aboard our meticulously maintained yachts equipped with all of the comforts of home.
If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II's relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis. Outdoors in nature, our sailing boat offers your choice of a ...
443-333-9113. Book Now. We offer private boat charters, from a few hours to overnight sails, certified sailing instruction and captain services in Annapolis MD and beyond! Sail with us!
Waypoints Yacht Charters offers personalized, full-service charter vacations from the world's best destinations, including the BVIs, Annapolis, Florida, and more. Skip to content. Book Now 443.225.4355. Book Now 443.225.4355. ... Annapolis Fall Charter Special. Get One Night FREE!*
Welcome Aboard our two beautiful, wooden 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Sunset is a favorite time for a sail on the Woodwinds. The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an ...
Admiral of the Bay is your premier nautical event planner; we specialize in Annapolis and Chesapeake Bay boat charters and sail boat charters. Sail boat and power boat charters for weddings, private and corporate parties, event planning on the Chesapeake Bay, Annapolis, Baltimore. Bareboat charters and bareboat rentals in Annapolis and on the Chesapeake Bay.
Rates and schedules are subject to change without notice. Our schedule may vary due to weather, special events, and group charters. Tickets go on sale six days prior to the date you want to sail. Please call our business office at 410-263-1981. Up-to-date schedule information is available by clicking here or calling (410) 263-7837.
We provide a community at the Annapolis Sailing School for your ongoing growth and enjoyment. We offer day sailboat rentals, adult sailing, KeelBoat Club Membership, KidShip sailing, powerboat lessons, and events at our beautiful location on Bembe Beach. Relaxed, but careful. The kids had fun with level one and enjoyed it all so much.
Annapolis Sample Itinerary. The Waypoints Annapolis base is in the heart of Annapolis right in the middle of the sailing capital of the world. The Chesapeake Bay, at about 200 miles long, is the largest estuary in the United States. There are coves and inlets all along the shoreline, small quaint towns to explore, and plenty of places to anchor ...
30+ Years Serving Chesapeake Bay Boaters. As a privately-owned company with over 30 years of experience, our reputation is based around the quality and our belief in first class customer service. Our friendly and knowledgeable team will help you choose the right boat and will also recommend destinations, activities, and enhancements to ensure ...
Annapolis Boat Shows will host the U.S. debuts of 12 state-of-the-art sailboats at its annual fall exhibition and sales show. These new models will join a lineup of 140 sailboats displayed at ...
The vessel was available for charter at a rate of $125,000 per week, and was often moored at the Annapolis Yacht Club, according to local media. View this post on Instagram.